Cesium carbonate → 4-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

HRID 12452

反応式

HRID 12452 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8](Br)=[C:9]([CH3:11])[N:10]=1)=[O:5])[CH3:2].[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:21]2[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[C:9]([CH3:11])[N:10]=1)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 59338079Ethyl 5-bromo-4-methylthiazole-2-carboxylate

生成物 1

HCID 593384494-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a solution of 5-bromo-4-methyl-thiazole-2-carboxylic acid ethyl ester (60 mg, 0.24 mmol) in 1,4-dioxane (2 ml) is added 1-naphthaleneboronic acid (50 mg, 0.29 mmol), cesium carbonate (187 mg, 0.58 mmol) and Pd(PPh3)4 (28 mg, 0.024 mmol). The reaction mixture is stirred in a sealed tube at 110° C. overnight. After cooling to rt, the mixture is purified by PTLC to give the title compound.

後処理

  1. temperatureAfter cooling to rt
  2. customthe mixture is purified by PTLC

出典と根拠

ORDレコード
ord-9f1c3eae5e914686a5941e976dd60d69
出典データセット
uspto-grants-2010_06
特許番号
US07728009B1

関連ノート

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